Abstract: The development of renewable vinyl-based photopolymer resins offers a promising solution to reducing the environmental impact associated with 3D printed materials. This study introduces a bifunctional lipoate cross-linker containing a dynamic disulfide bond, which is combined with acrylic monomers (n-butyl acrylate) and conventional photoinitiators to develop photopolymer resins that are compatible with commercial stereolithography 3D printing. The incorporation of disulfide bonds within the polymer network's backbone imparts the 3D printed objects with self-healing capabilities and complete degradability. Remarkably, the degraded resin can be fully recycled and reused for high-resolution reprinting of complex structures while preserving mechanical properties that are comparable to the original material. This proof-of-concept study not only presents a sustainable strategy for advancing acrylate-based 3D printing materials, but also introduces a novel approach for fabricating fully recyclable 3D-printed structures. This method paves the way for reducing the environmental impact while enhancing material reusability, offering significant potential for the development of eco-friendly additive manufacturing.
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N-[5-(1,2-Dithiolan-3-yl)pentanoyl]ethanesulfonamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With hydrogenchloride; sodium chloride; 1,1'-carbonyldiimidazole; In 1,4-dioxane; N-methyl-acetamide; water; mineral oil;
EXAMPLE 20 N-[5-(1,2-Dithiolan-3-yl)pentanoyl]<strong>[1520-70-3]ethanesulfonamide</strong> (Compound No. 1-497) STR34 500 mg of D,L-alpha-lipoic acid were dissolved in 10 ml of anhydrous dimethylformamide, and 428 mg of N,N'-carbonyldiimidazole were added to the solution, whilst ice-cooling. The mixture was then stirred at room temperature for 1 hour. At the end of this time, a solution of 284 mg of <strong>[1520-70-3]ethanesulfonamide</strong> in 3 ml of dimethylformamide and 113 mg of sodium hydride (as a 55percent w/w dispersion in mineral oil) were added to the reaction mixture, whilst ice-cooling, and the mixture was stirred at room temperature for 1 hour and then left to stand for 3 days. The solvent was then removed from the reaction mixture by evaporation under reduced pressure, and water and 2 N aqueous hydrochloric acid were added to the residue thus obtained to adjust the pH to 2, after which it was extracted with ethyl acetate. The extraction solution was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, and then the solvent was removed by evaporation under reduced pressure. The residue thus obtained was purified by silica gel column chromatography, using 1:1 and 2:1 by volume mixtures of ethyl acetate and hexane as eluent, followed by reverse phase preparative silica gel column chromatography, using 3:7, 2:3 and 1:1 by volume mixtures of acetonitrile and water as eluent. The solvent was then removed from the eluted fraction thus obtained by evaporation under reduced pressure, and the residue thus obtained was dissolved in dioxane. The solution was lyophilised, to obtain 30 mg of the title compound, melting at 98° C. to 100° C.
Example 8: Preparation of L-6-palmitoyl-2-alpha-lipoyl-ascorbic acid; 5.0 g of alpha-lipoic acid and 3.18 g of triethylamine were dissolved in 80 ml of methylene chloride. The reaction mixture was cooled to about -15C and then <n="23"/>3.16 g of ethyl chloroformate was gradually added thereto. The reaction mixture was stirred for 1 hour while the temperature was maintained and then further stirred at room temperature for 1 hour. The reaction mixture was cooled again to about -150C . A solution of 12.05 g of L-6-palmitoyl-ascorbic acid and 3.18 g of triethylamine in 100 ml of methylene chloride was rapidly added to the reaction mixture, which was then stirred for 2 hours while gradually increasing the temperature to room temperature. The resultant was concentrated under reduced pressure. 100 ml of a mixed solvent of n-hexane and methylene chloride (2:1 , v/v) was added to the obtained obtained oily residue. The reaction mixture was cooled to -50C and then filtered. The obtained crystal was dried to obtain 10.37 g of L-6-palmitoyl-2-alpha-lipoyl-ascorbic acid (yield: 71%). m.p.: 129-1320C1H NMR (400MHz, CDCI3), 4.89 (1H, s), 4.42-4.38(1 H, q), 4.36-4.22 (2H, m), 3.62-3.55(1 H, m), 3.23-3.10(2H, m), 2.65-2.61 (2H, t), 2.52-2.44(1 H1 m), 2.39-2.35(2H, t), 1.97-1.89(1 H, m), 1.79-1.43(8H1 m), 1.35-1.04(24H1 m), 0.90-0.88(3H, t)
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